Dimethylformamide → HCID 58917751, compound

Participants

Reaction Steps

Mix 5-formylindole (0.50 g, 3.4 mmol), 4-bromniomethyl-benzonitrile (0.74 g, 3.8 mmol), powdered potassium hydroxide (0.23 g, 4.1 mmol) and dimethylformamide (7 mL) in a flask. Stir at rt overnight. Pour into water (20 mL) and extract with EtOAc/Hexanes (2:1, 3×50 mL). Evaporate solvents to give a yellow oil. Purification on silica using a 10% EtOAc/Hexanes to 30% EtOAc/Hexanes gradient eluent yields the product (0.75 g, 83%). Mass spectrum (ion spray): m/z=259.2 (M−1); 1H NMR (CDCl3) 10.04 (s, 1H), 8.20 (s, 1H), 7.75 (d, J=8.6 Hz, 1H), 7.60 (d, J=8.2 Hz, 2H), 7.28 (d, J=8.5 Hz, 1H), 7.22 (d, J=3.1 Hz, 1H), 7.15 (d, J=8.2 Hz, 2H), 6.77 (d, J=3.1 Hz, 1H), 5.44 (s, 2H).

Provenance & Evidence